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Accelerating sulfonyl fluoride synthesis through electrochemical oxidative coupling of thiols and potassium fluoride in flow
Journal of Flow Chemistry ( IF 2.7 ) Pub Date : 2020-02-20 , DOI: 10.1007/s41981-019-00070-9
Yiran Cao , Benjamin Adriaenssens , Aloisio de A. Bartolomeu , Gabriele Laudadio , Kleber T. de Oliveira , Timothy Noël

Sulfonyl fluorides are valuable synthetic motifs which are currently of high interest due to the popularity of the sulfur (VI) fluoride exchange (SuFEx) click chemistry concept. Herein, we describe a flow chemistry approach to enable their synthesis through an electrochemical oxidative coupling of thiols and potassium fluoride. The reaction can be carried out at room temperature and atmospheric pressure and the yield of the targeted sulfonyl fluoride, by virtue of the short inter-electrode distance between a graphite anode and a stainless-steel cathode, reached up to 92% in only 5 min residence time compared to 6 to 36 h in batch. A diverse set of thiols (7 examples) was subsequently converted in flow. Finally, a fully telescoped process was developed which combines the electrochemical sulfonyl fluoride synthesis with a follow-up SuFEx reaction.



中文翻译:

通过流中硫醇和氟化钾的电化学氧化偶联促进磺酰氟的合成

磺酰氟是有价值的合成基序,由于硫(VI)氟化物交换(SuFEx)单击化学概念的普及,当前引起了人们的极大关注。在本文中,我们描述了一种流化学方法,可通过硫醇和氟化钾的电化学氧化偶联合成它们。该反应可以在室温和大气压下进行,并且由于石墨阳极和不锈钢阴极之间的电极间距离短,目标磺酰氟的收率仅在5分钟内达到92%停留时间为6至36小时(分批)。随后将多种硫醇(7个实例)进行了流动转化。最后,开发了一种完全伸缩的方法,该方法将电化学磺酰氟合成与后续的SuFEx反应结合在一起。

更新日期:2020-02-20
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